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Revision as of 14:59, 15 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|bu← Previous edit Latest revision as of 22:50, 11 December 2024 edit undoUninvitedCompany (talk | contribs)Bureaucrats, Administrators11,112 edits →See also: Ethanedisulfonic acid - preferred name 
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{{chembox {{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 444241662 | verifiedrevid = 450651119
| Name = Isethionic acid | Name = Isethionic acid
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Isethionic-acid-2D-skeletal.png | ImageFile = Isethionic-acid-2D-skeletal.png
| ImageSize = 180px | ImageSize = 180px
| ImageName = Skeletal formula | ImageName = Skeletal formula
| ImageFile1 = Isethionic-acid-3D-balls-B.png | ImageFile1 = Isethionic-acid-3D-balls-B.png
⚫ | ImageName1 = ball-and-stick model
| ImageSize1 = 200px
| ImageCaption1 = Isethionic acid
⚫ | ImageName1 = ball-and-stick model
| ImageName = Isethionic acid | PIN = 2-Hydroxyethane-1-sulfonic acid
⚫ |Section1={{Chembox Identifiers
| IUPACName = 2-hydroxyethanesulfonic acid
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | Section1 = {{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7578 | ChemSpiderID = 7578
| PubChem = 7866 | PubChem = 7866
Line 26: Line 25:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 107-36-8 | CASNo = 107-36-8
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 97J3QN9884
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 1157 | ChEBI = 1157
| SMILES = O=S(=O)(O)CCO | SMILES = O=S(=O)(O)CCO
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>2</sub>H<sub>6</sub>O<sub>4</sub>S | Formula = C<sub>2</sub>H<sub>6</sub>O<sub>4</sub>S
| MolarMass = 126.13 g/mol | MolarMass = 126.13 g/mol
| Density = 1.63 g/cm<sup>3</sup> | Density = 1.63 g/cm<sup>3</sup>
| pKa = 1.39 (predicted)
| MeltingPt = 191-194 °C
}} }}
}} }}


'''Isethionic acid''' is an ] containing an ]] located beta to a ]. Its discovery is generally attributed to ], who prepared it by the action of solid ] on ] in 1833.<ref name="Magnus1833">{{cite journal|last1=Magnus|first1=G.|title=Ueber die Weinschwefelsäure, ihren Einfluss auf die Aetherbildung, und über zwei neue Säuren ähnlicher Zusammensetzung|journal=Annalen der Physik und Chemie|volume=103|issue=2|year=1833|pages=367–388|issn=0003-3804|doi=10.1002/andp.18331030213|bibcode=1833AnP...103..367M|url=https://zenodo.org/record/1423558}}</ref>
'''Isethionic acid''' is a short chain ] ] containing ], is a ] solid used in the manufacture of mild, ] and high foaming anionic ]s for skin cleansing.<ref>{{cite web|title=Chemical land 21|work=Isethionic acid |url=http://www.chemicalland21.com/arokorhi/specialtychem/perchem/ISETHIONIC%20ACID.htm|accessdate=September 16, 2005}}</ref>
It is a white ] solid used in the manufacture of certain ]s and in the industrial production of ]. It is most commonly available in the form of its sodium salt (]).


==Synthesis==
⚫ The ]s ] and ] are available as diisethionates.<ref>{{cite book|title=Austria-Codex Stoffliste|editor=Wicho, H|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2009|edition=42|language=German}}</ref>
The original synthesis of the compound, involving the reaction of ] with ], has largely been replaced by more advanced methods. An alternative production method involves the hydrolysis of ], which is derived from the sulfonation of ].


:]
⚫ Synthetic isethionic acid is obtained from the reaction of ] with aqueous ], and is used for the industrial production of ].<ref>{{cite journal|first=Kurt|last=Kosswig|title=Sulfonic Acids, Aliphatic|journal=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|year=2000|doi=10.1002/14356007.a25_503|isbn=3527306730}}</ref>

However the most common route is the reaction of ] with aqueous ], which produces the sodium salt (]):

:]

==Reactions==
Isethionic acid is used as a starting material in the industrial production of ].

⚫ Dehydration of isethionic acid gives ].<ref>{{cite journal|first=Kurt|last=Kosswig|title=Sulfonic Acids, Aliphatic|journal=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|year=2000|doi=10.1002/14356007.a25_503|isbn=3-527-30673-0}}</ref>

===Derivatives===
] ] of isethionic acid (such as ] and ]) are used as ] anionic ]s.<ref name="Petter1984">{{cite journal|last1=Petter|first1=P. J.|title=Fatty acid sulfoalkyl amides and esters as cosmetic surfactants|journal=International Journal of Cosmetic Science|volume=6|issue=5|year=1984|pages=249–260|issn=0142-5463|doi=10.1111/j.1467-2494.1984.tb00382.x|pmid=19467117|s2cid=41819056}}</ref> These materials are much milder to skin that other sulfate based surfactants (i.e. ])<ref name="TupkerBunte1999">{{cite journal|last1=Tupker|first1=R. A.|last2=Bunte|first2=E. E.|last3=Fidler|first3=V.|last4=Wlechers|first4=J. W.|last5=Coenraads|first5=P. J.|title=Irritancy ranking of anionic detergents using one-time occlusive, repeated occlusive and repeated open tests|journal=Contact Dermatitis|volume=40|issue=6|year=1999|pages=316–322|issn=0105-1873|doi=10.1111/j.1600-0536.1999.tb06082.x|pmid=10385334|s2cid=418996}}</ref> making them popular for use in make-up, shampoos and detergent bars including those made by Dove.

⚫ Isethionic acid is also used as a ] in certain pharmaceutical ]s, including the ]s ] and ].<ref>{{cite book|title=Austria-Codex Stoffliste|editor=Wicho, H|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2009|edition=42|language=German}}</ref>


==Biological importance== ==Biological importance==
Studies made on dog heart slices suggested that heart tissue may be capable of converting ] to isethionic acid, further experiments demonstrated that this tissue may synthetize taurine from ].<ref>{{cite journal|author=W.O Read and J.D.Welty|year=1961|title=Synthesis of Taurine and Isethionic Acid by Dog Heart Slices|journal=The ]|volume=237|pages=1521–1522}}</ref> Studies made on dog heart slices suggested that heart tissue may be capable of converting ] to isethionic acid, further experiments demonstrated that this tissue may synthesize taurine from ].<ref>{{cite journal|author=W.O Read and J.D.Welty|year=1961|title=Synthesis of Taurine and Isethionic Acid by Dog Heart Slices|journal=The Journal of Biological Chemistry|volume=237|issue=5|pages=1521–1522|doi=10.1016/S0021-9258(19)83734-1|pmid=14490797|doi-access=free}}</ref>

==See also==
* ]
* ]


==References== ==References==
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